The startup world is often associated with youthful energy, fresh ideas and a seemingly boundless drive. However, after navigating the complexities of leadership for over two decades, I can confidently say that your 50s might just be the best time to dive into entrepreneurship as a woman leader.
In my early 50s, I was working as the head of sales in a high-pressure, fast-growing company, where I was expected to deliver results at any cost. The stress was relentless, and I felt increasingly disconnected from my work. One day, after being asked to manipulate my team to drive performance, I realised that I couldn’t stay on this path. That night, with no new job to go to, but understanding I needed a change, I resigned.
From there, I built my own consulting business, focusing on coaching small business owners and running workshops on leadership and strategy. This new venture allowed me to apply my years of experience in a more meaningful way, but came with its own challenges, particularly in marketing and self-promotion. However, my efforts paid off, and after a few years, I was approached to consult for a tech startup in the disability sector. My role quickly evolved and I eventually became their COO and, not long after, I was asked to step into the role of CEO.
Despite the challenges I’ve faced at the helm of The Chooze Shop, I have found that the Australian startup ecosystem is a unique and dynamic landscape where industry knowledge and a confident attitude can truly set you apart.
By the time we’re an older adult, many of life’s earlier responsibilities, such as raising children or climbing the corporate ladder, may have shifted, granting women unparalleled freedom to focus on entrepreneurial ventures. For me, this shift was transformative. I was no longer tied to the corporate grind and was free to make decisions that aligned with my values and long-term goals.
I’ve found there’s a certain confidence and clarity that comes from decades of professional and personal experiences. When I transitioned into my role as CEO, I drew upon every lesson I’d learned over the years. From managing stress in high-pressure situations to making tough decisions that affected the entire team, my past experiences became invaluable tools.
By our 50s, we’ve learned to trust our instincts and stand by our decisions without being overly concerned about others’ opinions. We’ve been through the highs and lows, the successes and the failures, and these experiences have shaped us into leaders who can handle the pressure of the startup world. We know what works, and what doesn’t, and we’re not afraid to make tough calls.
One of the most significant advantages of leading a startup at 58 is the extensive industry experience you’ve accumulated. My years spent in various leadership roles gave me a deep well of knowledge to draw from, allowing me to anticipate challenges before they arose and guide the startup through critical decisions. As we age, we cultivate a more strategic approach grounded in years of practical experience, shaped by years of navigating various professional landscapes. It ensures that we’re not just dreaming big, but also delivering on those dreams.
As older adults, our maturity is reflected not only in our perspective, but in the strength of our professional networks. Overtime, we build robust relationships that can be leveraged for partnerships, mentorships and strategic alliances—assets that younger leaders can sometimes lack. As a CEO, the professional networks I have built over decades are invaluable, opening doors that would have been out of reach for my younger self.
Transitioning into the CEO role also meant gaining the confidence of investors. My age and experience, which I initially viewed as hurdles, quickly became strengths. From an investor’s perspective, older leaders offer a level of stability that may be harder to find in younger entrepreneurs. The networks I had cultivated facilitated key partnerships and opened the door to top talent, accelerating our growth trajectory and cementing investor confidence.
The wisdom accumulated over the years equips us with the strength to handle the inevitable ups and downs of startup life. Investors are drawn to a track record of success and as an older adult, your seasoned judgement provides a level of predictability and security that is invaluable during tough times. This resilience can be a calming influence on the team and attractive to investors who value stability in a high-risk environment.
Even with decades of experience, impostor syndrome can still rear its ugly head. It’s easy to feel like you’re not equipped to compete with younger, seemingly more adaptable leaders. This feeling can be exacerbated by ageism, which, according to a recent report, remains a pervasive issue in Australian workplaces.
As mature women, many of us have experienced the feeling of becoming invisible, undervalued, or overlooked for job opportunities, promotions and pay rises. Older women leaders are not always well represented in the startup ecosystem, which can exacerbate feelings of isolation or inadequacy. My advice?
Draw on your experience: Don’t let self-doubt take over. Draw on the skills you’ve honed over the years, reflecting on the good things, as well as the monumental failures, as motivation to push through.
Stay relevant and connected: Engage in industry workshops, take online courses, and attend webinars to keep up with the latest tools, trends and technologies so you’re not just keeping up; but leading the way.
Build your personal brand: Establish yourself as a thought leader by sharing your expertise through blogs, podcasts, and social media and maintain a dynamic LinkedIn profile that reflects your accomplishments
Become a mentor: Take the time to mentor younger team members, fostering a culture of learning and growth. This not only benefits your team, but also demonstrates that you are committed to nurturing talent.
Blaze your own trail: There’s something to be said for the ‘less shits given’ attitude that comes with age. Embrace the fearless, authentic leadership that comes with experience, take bold risks, and innovate without inhibition.
My journey has shown me that it’s never too late to embrace your power. Lean into your experience, stay curious, stay connected, and lead with the confidence that comes from knowing your worth. And just remember, when the road gets tough (and trust me, it will), it’s your resilience, your tenacity, and all those lessons learned along the way that will help you push through and come out stronger on the other side.
This is your moment, so grab it and lead with all the brilliance and boldness that only experience can bring.
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